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Adamantyl pyridinecarboxamide complex as well as intermediate, preparation method and application thereof

A technology of adamantyl pyridine carboxamide and complexes, which is applied in the direction of copper organic compounds, drug combinations, anti-toxins, etc., and can solve the problems of easy hydrolysis by protease, high cost, and difficult extraction of SOD

Inactive Publication Date: 2014-07-23
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is that the purpose of the present invention is to overcome the shortcomings of natural superoxide dismutase natural SOD in the prior art, such as difficult extraction, high cost, easy to be hydrolyzed by protease, difficult to penetrate cell membrane and heterogeneous antigenicity, and provide A SOD mimetic enzyme with adamantane and pyridinecarboxamide structures that is easy to prepare, low in cost, efficient and easy to permeate the cell membrane, that is, the adamantylpyridinecarboxamide complex, and at the same time provides the adamantylpyridinecarboxamide complex The preparation method and application of the compound also provide an intermediate for the preparation of the adamantyl pyridine carboxamide complex and a preparation method thereof

Method used

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  • Adamantyl pyridinecarboxamide complex as well as intermediate, preparation method and application thereof
  • Adamantyl pyridinecarboxamide complex as well as intermediate, preparation method and application thereof
  • Adamantyl pyridinecarboxamide complex as well as intermediate, preparation method and application thereof

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preparation example Construction

[0054] In the preparation method of the above intermediate, in order to increase the yield of the contact reaction, preferably the contact reaction is carried out below 0°C, and the reaction temperature of the contact reaction is -10-0°C, preferably -3-0°C;

[0055] According to the present invention, in order to make the contact reaction fully proceed, the reaction time of the contact reaction is 3-20 h, preferably 10-15 h.

[0056] [ M(N3) 2 ]·6H 2 O carries out complex reaction;

[0057]

[0058] In formula (L1), n ​​is 1-3, preferably, n is 1;

[0059] In the above formula, M is a divalent metal cation, and N3 is selected from perchlorate ion, hexafluorophosphate ion or tetrafluoroborate ion;

[0060] Preferably, M is Cu 2+ or Zn 2+ , N3 is perchlorate ion;

[0061] More preferably, the [M(N3) 2 ]·6H 2 O is Cu(ClO 4 ) 2 ·6H 2 O.

[0062] According to the present invention, the organic solvent only needs to be an organic solvent capable of dissolving the rea...

preparation example 1

[0072] Preparation of 1-adamantanyl chloride:

[0073] In a 250mL round-bottomed flask, add 10.0mmol of 1-adamantanecarboxylic acid solid and 60mL of anhydrous toluene solvent in sequence, and slowly add 20mL of thionyl chloride dropwise after magnetic stirring to dissolve, reflux at 80°C for 8 hours, and cool to 20°C , the solvent was removed by rotary evaporation, and 10 mL of anhydrous toluene was added three times, and the solvent and excess thionyl chloride were removed by rotary evaporation to obtain a light yellow crystalline powder.

Embodiment 1-1

[0075] The preparation of the intermediate of structure shown in formula (L2):

[0076]

[0077] In a 100mL round-bottomed flask, at 0°C, add 5.0mmol of 1-adamantanyl chloride and 25mL of anhydrous toluene in sequence. After magnetically stirring to dissolve, add 10mmol of anhydrous potassium carbonate, and slowly add 2-methylaminopyridine 6.3 mmol, react under ice-bath conditions for 12 hours, filter, and obtain 1.154 g of light yellow crude product after removing the solvent by rotary evaporation under reduced pressure. The crude product was recrystallized from a mixed solvent of ethyl acetate and ether to obtain a white powder. Recrystallized in a mixed solvent of ethyl acetate and petroleum ether (v / v=1:3) to obtain 1.050 g of white powder with a yield of 76%. Its detection data are as follows.

[0078] The white powder was subjected to elemental analysis, and the result was C 17 h 22 N 2 O: C, 75.36%; N, 10.18%; H, 8.47%; Theoretical calculation value: C, 75.52%; ...

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Abstract

The invention discloses an adamantyl pyridinecarboxamide complex as well as intermediate, a preparation method and application thereof. The structure of the complex is as shown in the formula (I), wherein n is 1-3, M is a divalent metal cation, N is one of perchlorate ions, hexafluoro-phosphate radicals or tetrafluoroborate radicals. The complex provided by the invention or the complex prepared by the method has an excellent activity of catalyzing superoxide disproportionation. The formula (I) is as shown in the specification.

Description

technical field [0001] The invention relates to an adamantyl pyridine carboxamide complex, an intermediate for preparing the adamantyl pyridine carboxamide complex, a preparation method and application of the adamantyl pyridine carboxamide complex and the intermediate. Background technique [0002] The medical community generally believes that free radicals are the main cause of human aging and neurodegenerative diseases. Modern medicine has confirmed that excess superoxide ion free radicals (O 2 · - ) can lead to human aging and diseases such as cancer, cardiovascular and cerebrovascular diseases, and amyotrophic lateral sclerosis. Superoxide dismutase (SOD) removes O 2 · - The specificity of the enzyme, known as "human body scavenger", is used in clinical medicine to treat various diseases such as Alzheimer's disease and tumors, and is also widely used in skin care products and health care products. However, the natural SOD has the disadvantages of difficult extractio...

Claims

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Application Information

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IPC IPC(8): C07F1/08C07D213/40A61P39/06
Inventor 周映华陈丽晴孙大亮
Owner ANHUI NORMAL UNIV
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